Doug and Cindy
by Karen Shane
I
Hesitantly Doug entered the shop. He was nervous and was sure everyone
was watching him. But, as he looked around he saw nobody paying any
attention to him so he stepped farther into the little boutique. It
was a specialty shop and Doug was sure he could get what he needed
here. It had taken him a long time to work up the courage to get this
far and he wasn't going to back down now.
"Can I help you?" said the pretty young sales clerk.
"Uh, well, I'd like to look around first," Doug responded.
"O.K., just call if you need any help, I'll be right over here if you
need anything." And the clerk turned and left him to wander around the
store by himself.
Dougs heart was pounding as he drifted among the isles of clothing. He
had always wanted to check out this tall girls shop but he had been too
afraid in the past. Now he was determined to go through with it, and
he had the hardest part over. He was in the store now and nothing
would stop him from completing what he had set out to do today.
Towards the back of the store Doug found what he had been looking for,
the lingerie section. He quickly selected a Platex
Thank-Goodness-It-Fits brassire in size 38 nearly B. He looked at the
package and made sure it was the right bra. It was, and it was in the
color he wanted, black, so he turned to the next isle.
He found the Platex panty girdles and picked out a thigh high style and
made sure it was size 7. With both foundation boxes under his arm he
looked around a little more and found some pretty lace trimmed garter
belts. He picked one out with red satin trim and added that to the
growing collection of packages.
Next he journyed deeper into the store and began examining the rack
containing slips. He selected a black lace trimmed nylon tricot slip
in size 38 tall. After assuring himself that it would fit properly he
picked out a pair of sandlewood nylons stockings and headed for the
sales counter.
"Did you find everything you wanted?" Inquired the pretty young girl.
Doug stammered for a second, cleared his throat and then said, "Uh, I
think so. Perhaps you could recommend a nice inexpensive outfit to
complete this ensemble."
The clerk looked up from the sales tickets she had been checking and
examined the items he had placed on the counter. "Well, let's see now.
Pretty underthings here deserve a pretty dress. Did you want a skirt
and blouse, or is a dress more in line with what you had in mind?" she
inquired.
"I really hadn't thought about that," Doug returned, "What do you
suggest?"
The clerk was making her way through the isles and Doug followed close
behind. He had left the other articles on the counter and was startled
when the girl turned and held a dress up next to him and said, "This
would look pretty with what you've already picked out."
Doug turned red as she held the dress against his body. He wanted to
protest, but could not find the courage to deny what the clerk had
infered. The clerk noticed his embarassment and tried to ease it
somewhat, "Don't worry. We get lots of men in here who like the items
we sell. If it does'nt bother me, why let it bother you."
He thought about it for a minute and felt a little better with her
confiding in him in such a frank manner. "Well, it's just that I
never, well..., I mean I never...,"he stammered.
"Don't worry about it. If you'd like, you can try everything on in
back. We have a special room and no one will disturb you."
Doug couldn't believe what he was hearing. "Uh, are you sure?"
She drapped the dress over her arm and said, "Come on, follow me." Then
she turned and headed back to the counter and picked up the other
packages he had selected earlier. She continued on to a curtain
hanging at the back of the store and held it open for him.
Doug stepped through and then the clerk entered and pointed towards
another door. "Right in there, no one will disturb you. If you need
any help, just press the little buzzer and I'll come back and help
however I can." With that she handed him the dress and other articles,
turned and left Doug standing there by himself.
Hesitantly, he thought about it and then hurried to the door. As he
pulled the door open he was somewhat surprised to find such a large
dressing room. Inside he found that he could bolt the door and he
quickly did so. He crossed over to the dressing table and laid the
items down.
Doug looked around the room and found that in addition to the dressing
table, there was a stand with half a dozen different wigs and another
dressing table with all kinds of make up on it.
He quickly removed his clothing and hung them from a hook next to the
table. Standing there naked he began to shake as he removed the lycra
panty girdle from its box. He had selected the thigh high type to help
hide his maleness and quickly pulled the garment from the box.
Nervously he put one foot into the panty and then rapidly slipped the
panty over his other foot. Before pulling the garment up he pulled his
testicles back between his legs and pressed his thighs together to hold
them there.
He then pulled the panties up and adjusted them to the contours of his
body. Next he removed the brassire from its carton and noticed his
hands were shaking badly. He had a little difficulty fastening the
clasps because of shakiness, but managed to get them hooked properly.
He removed the slip from its hanger, pulled off the tags and then slid
it over his head. The feeling of constriction from the bra and panty
girdle gave him a sense of pleasure. The coolness of silk against his
body from the slip sent shudders of delight throughout him.
Before trying on the dress he admired his own reflection in the mirror
and marveled at how well he could mimic the female form. He was
delighted with what he saw and then picked up the dress from the table.
After unzipping it full length, he stepped into the dress and then
adjusted the shoulders and bust to his figure.
With difficulty he managed to get the zipper all the way back up and
was just admiring the fit when he heard a knock at the door. He
recognize the clerks voice when she said, "If you're ready, I've picked
out a couple of accessories that will go very nicely with that outfit."
Doug was scared! He hadn't planned to try the things on in the store.
And now here he was completely dressed in the clothes he had been
wanting so long and someone was at the door. Slowly he stepped over to
the door and drew the bolt back.
The young clerk briskly entered the room and placed some jewelery items
on the table. "My but that's a pretty outfit. I'll bet you'd really
like to wear those things out of here."
Doug was too stuned. "I don't think that's possible. I'd get into
trouble for sure."
"Well listen," she continued, "I'll be closing the shop in a few
minutes and you can come by my place. Here, try a couple of these wigs
on and I'll be back in a few minutes." With that she left Doug alone to
ponder what had just happened.
He picked up the necklace she had left on the table and fastened it
around his neck. After slipping the braclet on his wrist he realized
he had not tried on the nylons or garter belt yet so he pulled up his
dress and slip and fastened the flimsy garment around his waist.
Doug removed the nylons from the container and gathered one up in a
ball and slowly fitted it to his leg. After hooking the garters to it
he began to put the other one on and was just fastening it when the
clerk returned. Since he had forgotten to bolt the door after she had
departed, she walked in as he was fastening the other nylon.
"Here," she said as she crossed the room to him "always hook the straps
through your panties. That way if you need to take your panties down,
you don't have to undo everything." With that she unhooked the garters
and threaded the straps through Dougs panty. After she had it properly
adjusted she reattached it to the nylon and saw that he was finishing
the other nylon.
He quickly dropped the slip and smoothed the dress down as the clerk
selected a pretty auborn wig and removed it from its stand. "Let's try
this one," she said as she motioned for him to set down in the chair in
front of the dressing table.
Doug meakly obeyed and she expertly fitted the hair piece in place.
After adjusting the wig, she stepped back and allowed him to see the
full effect in the mirror. He could not believe what his eyes saw.
The reflection in the mirror was beautiful! Even without make up the
red head returning his gaze from the mirror looked ravishing.
As the clerk picked up a stick of foundation make up she said, "My
name's Cindy. What's yours?"
"Doug," he responded quietly as she began smoothing the foundation on
his face and neck. Quickly and expertly she blended the make up in
with her finger tips and then selected a light green eye shadow for his
eyes.
"Green will go good with that wig," Cindy stated as she brushed the
light powder on his eyelids. "We don't want to overdo it though.
Here, see if you can apply this lipstick properly," she said as she
handed Doug a tube of rose petal lip gloss.
Slowly and carefully he traced the outline of his lips with the tube
and then pressed his lips together. When he finished Cindy was holding
a small kleenex for him to blot his lips with. "Thanks," he said as he
took the kleenex and completed the task.
Cindy picked up a brush and made minor adjustments to the wig as she
inquired, "Have you been doing this long?"
Doug answered tentatively, "Privately I've enjoyed dressing as a woman
for a couple of years now. But this is the first time I've ever had
the opportunity to share it with anyone else. That's why I came to
this boutique. I wanted to make sure I got everything in the right
size. I must admit, I was quite surprised with how well you put me at
ease in here."
"We get lots of guys in here that are into womens clothes, but you're
the first one I've ever given special attention to," she said.
Cindy finished with the brush and was satisfied with the look. "One
last thing, we'd better get some shoes for you. Follow me and we'll
try a couple pair on." She headed for the door and Doug followed after
taking one last look in the mirror.
Amazing he thought, absolutely amazing. He followed her out the door
and back to the store. Cindy was standing near the shoe department and
asked him what size shoe he wore. Doug told her the male size he
normally bought and she went over to a rack and pulled a box down.
"Here, let's try these," she said as she opened the box and removed a
pair of woven straw sandels.
Doug sat down and slipped the sandels on. It took him a second to
figure out how the straps laced around his ankle and then he buckled
them and stood back up. "Perfect," he said as he admired them in the
floor mirror.
"Come on then, let's go. I'll get your other things and put them in a
bag. You can change back if you want to at my place." With that Cindy
disappeared in the other room for a minute and then reappeared with a
boutique plastic bag in hand. Doug followed her as she headed for the
door and waited patiently outside as she turned the key in the lock and
dropped the keys in her purse.
"I'm parked right around the corner. Let's go across the street for a
quick drink before we take off."
"Gee, I don't know if I'm ready for all this. Maybe we'd better just
get going," he said.
II
Doug woke from the dream covered with persperation and with a
tremendous hard on. He was in his own bed and could sense his wifes'
body next to him. He thought about the dream and could recall every
detail as if he had really lived the experience. It disturbed him that
he had had the dream again. This was the third time this week alone
and each time it was the same.
If only he could see how the dream ended he thought. Or better yet, if
he could really experience it. Doug got up from the damp bed and
quietly padded out to the kitchen. As he prepared the coffee pot for
the morning ritual, he lit a cigarette and pondered the dream again.
The aroma of caffine invaded his nostrils and Doug snubbed out the butt
as he reached for a cup. While pouring the hot liquid he heard Cindy
stirring in the bedroom and knew she would soon be joining him.
"Have that dream again?" Cindy inquired as she joined him at the
kitchen bar. She was the image of his perplexing nocturnal adventure
and he only nodded affirmatively as he avoided her gaze. "Come on
honey, talk about it. It might help if we can work it out together. I
love you dear."
"I don't understand it Cindy," he started, "Why am I having this same
reoccuring dream? What does it all mean?"
"Doug, I love you very much. Maybe if we actually acted out the dream,
it wouldn't bother you anymore." Cindy peered deeply into his eyes
questioningly as Doug turned toward her.
He considered her suggestion and then responded, "I really don't know.
We've been married for two years now and why does something like this
start affecting me so much? I'm no homosexual and I've never had
thoughts like this before. Why now," he inquired.
"Look," Cindy began, "it's friday and we have the weekend ahead of us.
Let's make reservations at a motel in town and just get away from here
for awhile. The change will be good for us. And," she lingered for a
minute, "perhaps we can explore this a little farther."
Doug considered the idea and then stated, "I'll call from work and make
the arrangements. Maybe you're right." As he got up from the bar and
started for the bathroom to get ready for work Cindy hugged him tightly
and placed an affectionate kiss on his ear lobe.
Doug put the dream from his mind and quickly showered. Cindy was busy
in the bedroom when he left for work and the rest of the day was quite
normal for him. During his lunch hour from the parts department he
worked in, he called and made the reservations at a Holiday Inn on the
outskirts of town. "Maybe Cindys' right," he muttered to himself as he
hung up the phone.
Doug arrived home shortly after five o'clock to find Cindy waiting in
the living room with three suitcases setting next to the door. "What's
this?" he inquired.
"I hope you didn't forget to make reservations. These are our bags,
let's go." With that, Cindy grabbed one of the traveling cases and
headed out the door.
Half an hour later the two were climbing the carpeted stairs to their
room at the motel. As Doug placed the luggage on the traveling stand
Cindy darted into the bathroom and said, "I'll get a bath ready for you
and then call room service for a few drinks while you relax and unwind
from the day."
Doug nodded and absent mindedly flipped on the television set. A few
minutes later Cindy reappeared and informed him every thing was ready.
Entering the bathroom, he noticed she had drawn a hot bubble bath for
him and had placed his shaving gear on the counter next to the sink.
After removing his clothes and easing into the foamy liquid, Doug heard
her requesting a bottle of champagne from room service.
Cindy came into the bathroom and sat on the edge of the tub. She let
her hand slip into the warm water and slowly swim its way towards
Dougs' naked thigh. Just as she made contact with his groin they both
heard a knock at the door. "Must be room service," Cindy said as she
stood and scooped up the clothing Doug had dropped on the rack above
the toilet.
Cindy had pulled the bathroom door shut when she opened the door to the
hallway to allow the bellhop to bring in the cart with the champagne.
After thanking the bellhop she handed him a twenty dollar bill and
said, "I'd really appreciate it if you could dispose of these items
immediately." With that she handed the bellhop the clothing she had
brought from the bathroom with her.
The bellhop smiled quickly as he tucked the bill in his pocket and took
the articles she held in his direction. He then disappeared as she
closed the door behind him and locked the door.
Cindy carried the champage and two glasses back into the bathroom and
sat them on the floor next to the tub. She removed her blouse and
skirt and tossed them out onto the bed as she lowered herself to edge
of the tub again.
Doug admired her ample breast and the way they strained at the skimpy
brassire she was wearing. Cindy filled the glasses with the bubbely
liquid and then handed one to Doug. As he started sipping the drink,
Cindy picked up the razor from the counter and lowered it into the tub.
Doug looked at her inquisitively as she reached into the water with her
other hand and grasped his ankle.
"Enjoy every minute of this, Doug. I love you and want you to be as
happy as I can make you." Cindy said as she slowly began drawing the
razor along his leg. Doug started to protest but she merely handed him
another glass of champagne and continued with her task.
Moments later she had finished one leg and was busy with the other
while Doug helped himself to another drink. When she stopped to admire
her handiwork, she noticed he had dozed off and was sleeping with his
arms folded behind his head. Carefully and ever so gently she began
shaving his underarms and was able to complete the task without
awakening him. Satisfied that she had done properly, she left Doug nap
a little longer while she went into the other room and set about
arranging the rest of her surprise for him.
Doug opened his eyes and felt Cindy massaging his flacid penis. The
water was now tepid and most of the bubbles had dissapated. "Boy, I
must have really been tired. How long have I been in here?" Doug
asked.
"Not long, honey. It's a little past eight. We ought to get dressed
and go down to the lounge for something to eat. Come on and I'll help
you." Cindy stood and handed him a towel. Doug quickly dried off and
then followed her out of the bathroom.
Looking around the room, Doug was unable to find any of his clothing.
He picked up each suitcase and noticed they all felt empty. "What'd
you do with my things?" he inquired.
"Everything you wore in here is gone. I've packed enough for us for
the weekend." With that, Cindy handed Doug a pair of pastel lycra
spandex panties and watched the expression on his face. Slowly the
look of terror was replaced with a peaceful smile as he reached out and
took the garment from her hand.
Tentatively Doug placed one foot in the panty and then quickly stepped
into them with the other foot. As he began pulling the slinky fabric
up his body he felt a sense of urgency compelling him onward.
After adjusting the hiphuggers, Doug looked at Cindy and noticed she
was holding a matching brassire for him. He put out his hands to
accept the bra and Cindy threaded it over his hands and up his arms.
As he positioned the boned-underwire cups to his chest, Cindy cinched
the garment from behind and hooked the clasps.
Doug admired her selection. The bra fit very comfortably. It was a
deep plunge, underwire affair with strech straps and lace trim
everywhere. Before he could inspect the garment any farther, Cindy was
wrapping a combination garter belt, waist cincher around his
midsection.
It too, he noticed, matched the pastel panties and bra. On each of the
elastic garter straps was a small silky ribbon hanging from a little
ribbon bow. Cindy had finished hooking the hooks and was trying to zip
up the zipper. "You'll have to hold your tummy in as much as possible.
I got this a little tight in order to give you a little better figure."
She said.
Doug had a hard time believing what was happening, and, he had an
equally hard time holding his stomach in enough for Cindy to get the
girdle affair zipped up. But somehow she managed and then stepped
around in front of him.
She started threading the garter straps through his panties and Doug
was quick to follow suit with the other leg. After the eight dangling
straps were properly adjusted by Cindy, she handed him a pair of smoke
colored nylons and then went over to the dresser.
Doug was busy sliding the smooth silk up his freshly shaven legs and
didn't notice Cindy removing the wig from a hat box. He was enjoying
the slick feeling the material produced against his bare legs. As he
donned the second nylon he became accutely aware of the erection
between his legs. The feel of slippery legs, the underwire bra and the
constriction of lycra spandex panties were too much for him.
"I thought that might happen." Cindy said as she observed Dougs
prediciment, "so I've got a little idea how to handle that problem."
Cindy crossed the room to Doug and rolled his panties down. She then
stepped behind him and reached through his legs and grabbed his
testicles. As she tugged them back she forced his rigid cock back and
held it against the two smaller sacks. Next she applied pieces of
surgical tape to the head of his penis and pressed the ends to his
crotch. She put one more long piece of tape across the length of his
hard on and pressed the end of it deep into his anus.
"O.k., now adjust your panties and I'll bet that'll take care of it,"
she said.
Doug pulled the panties back up and smoothed them in place. He
couldn't help but admire the appearance of a feminine pubic mound and
glanced at Cindy. She was smiling at the effect of her handiwork and
said, "Here, put this slip on and we'll see what a little make up will
do." With that she handed him a dainty satin slip of the same pastel
color.
Doug quickly slid the slip over his head and let it drop down his body.
He liked the way the lace trim bodice drapped over his bra, and the way
the cool, soft fabric felt. As he smoothed the garment in place with
his hands his body became charged with a tingling sensation.
Cindy had him set in a chair beside the dressing table while she sat on
the edge of the bed and began by trimming his eye brows with a small
pair of tweezers. After she had thinned them considerably she picked
up a styling pencil and lightly filled out a soft, feminine arch.
After completing the eyebrows, Cindy dabbed small amounts of light aqua
colored powder to the tops of his eyelids and then blended it with a
cotton swab. Next she applied a Cover Girl foundation to his cheeks,
forehead, chin and neck. She also blended this with a cotton ball and
then applied a light coating of powder to the same areas.
When she was satisfied with the softness of the skin texture, she
applied a thin coating of blusher to his cheeks and used her fingers to
fade the edges of the blusher. Happy with the effect she was creating,
Cindy removed a mascara wand from her make up case and applied a thin
coat to Dougs eye lashes.
She sat back on the bed and admired her handiwork. "Damn, you're
pretty," she remarked. Doug turned towards the mirror and gasped at
how beautiful and womanly he had become. It was difficult for him to
imagine that beneath the reflection staring back at him was really a
man.
Cindy handed Doug a pair of silver clip on earrings to put on while she
fastened a matching silver necklace around his neck. When she finished
with the necklace she bent down and hooked a smaller version of the
necklace around his left ankle.
"Just a few more details and we'll be ready, honey." She said as she
produced a dark brown wig Doug immediately recognized from her
collection of wigs at home. She slipped the trusses over his scalp and
fitted it to his head. With a small styling brush she teased a few
curls into place and patted a few others with the palm of her hand.
"After you have your dress on, we'll take care of your hands and then
we can go." Cindy then pulled a beige ruffled blouse from the hangers
she had previously hung in the closet and helped Doug into the garment.
As she buttoned the buttons in back, he straigtened the collor and
fluffed up the ruffles in front.
Doug glanced in the mirror and noticed the ruffled blouse created the
illusion of a larger bust line than he actually had. He turned back to
find Cindy holding a tweed, straight skirt for him to step into. He
pulled the garment on and Cindy zipped and fastened the clasps in back
for him. As he reached under the skirt to adjust his slip, Cindy
retrieved the matching jacket from another hanger and handed it to
Doug.
After tucking his blouse into the skirt, Doug slipped into the jacket
and turned to admire himself in the mirror. Cindy handed him a package
and said, "Here, see if you can put these plastic finger nails on while
I get dressed." She then disappeared into the bathroom while he tore
open the package.
When he finished with the nails, Doug walked around the room and
enjoyed the feel of female garments swaying against his body. The
sensations were electric and he felt ecstatic. He was still enjoying
the slick nylon charge when Cindy stepped out of the bathroom dressed
equally as beautiful as he was.
She stepped into a pair of patent leather spiked heels and said,
"Perhaps you'd better wear these lower heeled slippers. It takes a
little getting used to walking around before you'll be able to handle
high heels." She then handed him a pair of beige leather low heeled
slippers and he quickly slipped them on his nylon covered feet.
Doug stood before her; both the picture of feminity. She stepped
closer and hugged him tightly. They kissed passionately and both could
sense the arousal in the other. Cindy pulled away from the embrace and
said, "Now for the lipstick and we're ready to go. You can carry this
little purse for effect and I'll take mine along with everything we'll
need." She handed Doug a tube of pale pink lipstick and watched as he
traced it on his lips. When he finished applying it, she gave him a
small beige handbag and he placed the lipstick in it.
She picked up her purse and opened the door. "Well, let's go to the
lounge and get something to eat. I'm famished." Doug followed her out
the door and stood in the hallway as she locked the door.
Pangs of guilt and apprehension invaded him as another couple appeared
down the hall. Cindy saw the fear in his eyes and quickly linked her
arm in his. "Believe me darling, no one but I know who, or what you
really are. Come on, let's go."
III.
Cindy led him down the hallway and could feel his sense of confidence
returning. The closer they got to the stairway, the more she could
tell he was loosening up and begining to enjoy the experience.
"I'll do the ordering as your voice may give you away." They descended
the stairs and crossed the lobby to the lounge. Doug glanced about and
noticed the clerks paid them no mind. A few guest mingled in the lobby
and they too paid no attention to the two well dressed women headed for
the lounge.
The hostess guided them through the dimly lit bar to a small table near
the rear of the lounge. Before departing she accepted Cindys order for
drinks and then disappeared amid the tingle of glasses and music from
the band.
Soon their waitress delivered the drinks and Cindy selected entrees
from the menu for them both. Before their meal arrived, the waitress
brought another round of drinks and said, "The gentlemen next to the
bar hope you'll accept these with their compliments." She nodded
towards a table with two well dressed business men and sat the glasses
down.
Doug and Cindy both glanced toward the men. Cindy smiled and tipped
her glass in the air to the men and then turned back to Doug. "See, I
told you no one could tell but me."
Doug felt a little nervious and wispered to her, "What do we do if
someone trys to hit on us?"
"Honey, this is your fantasy. Enjoy it. Just do what ever comes
naturally. But when it's all over, we're the ones that are together."
Doug smiled at Cindy and rubbed his knee against hers under the table.
The feel of nylon against nylon excited them both and Cindy responded
by slipping her hand beneath the table cloth and placing it on his leg.
As he finished his drink she slowly slid her hand up his leg and toyed
with the top of his nylon. Doug felt the tension of his garter strap
as she traced the outline of the fastening. He also felt his growing
erection and was thankful Cindy had been so thorough in taping his
member back.
When their meal arrived, Cindy ordered another round of drinks and both
attacked the food with a passion. As they finished the dinner Doug saw
the two gentlemen head toward their table. He pressed his knee against
Cindys and indicated for her to look in their direction.
Cindy looked up as the two arrived at the table. She smiled demurely
as the taller of the two asked her, "Would you two young ladies care to
dance?"
The music was slow and so was she in responding, "Why, I think we'd
love to. Wouldn't we Darla?" She looked directly at Doug when she said
that and could tell he was nervous. Then she accepted the outstreched
arm of the shorter of the two men and accompanied him to the dance
floor.
"Darla, eh? Pretty name, shall we join them?" said the huskier fellow.
Doug placed his hand on the mans arm and slowly stood up from the
table. The two made their way between the other tables and were soon
on the dance floor.
Fighting instinct, Doug allowed the man to place his arms around him
and then tried hard to follow his lead. As if it came naturally, Doug
found out he had no trouble assuming the proper role and soon the two
were tightly pressed together.
The music drifted among them as Doug became keenly aware of the bulge
in his partners pants. He found it exciting that another man was
becoming turned on by him and he increased the pressure of his own
pelvic area against his partner. The two danced slower, while Doug
sensed the urgency of his own masculine appendage.
Rythmatically he began pressing his hips harder and harder against his
dance partner. The husky gentlemen responded with equal pressure and
Doug found himself placing his head deeper into the mans shoulder.
As they continued to dance, Doug became very aware of the mans hand
pressing more firmly against his back. He could feel his partners hand
against the hooks of his bra and this only excited him more. He did
not realize the music had stopped when he felt the mans hand slid from
his back and drift across his buttocks.
With a meaningful pat on Dougs feminine derrire, the man said, "We'll
have to do it again, Darla." And as a gentleman, he escorted Doug back
to the table.
Doug pursed his pink lips and smiled affectionately at the gentleman as
he retook his seat. Cindy was now joining them and her partner asked,
"How 'bout if we join you two and make an evening of it?"
Doug nervously pulled a cigarette from Cindys purse and placed it in
his lips. He was searching for the lighter when his dance partner
offered a light. As he puffed on the cigarette he heard Cindy feign an
excuse of returning to awaiting husbands upstairs and the two men
reluctanly bid farwell and departed.
Cindy signaled the waitress for the check and told Doug, "I think it's
time the two of us get out of here." Doug nodded eagerly and departed
with her after she had signed the room number to the tab.
They arrived back in their room minutes later without incident and
Cindy was only too happy to kick off her shoes and sink into the bed.
Doug retrieved the champagne from the bathroom and poured them both a
drink.
"Well, what did you think of your dream now that you've had a chance to
act it out?" Cindy inquired.
"It was a little scary at first. And then when those guys asked us to
dance, I nearly died. Do you know he got a big hard on and kept
rubbing it against me."
Cindy chuckled and said, "Well can you blame him. Look at yourself,
you really are a beautiful woman. But right now I want that beautiful
woman to climb on top of me, or better yet," she hesitated, "I'd rather
climb on top of that beautiful woman."
Doug dropped to the bed and the two clung desperately together.
"Wait," Cindy said, "let's shed a little of this clothing first. I've
got another surprise for you."
With that she hopped up from the bed and crossed the room to the
closet. Deftly she removed two identical floor length satin pegnoir
sets and returned to the bed side. "Take everything from your slip on
out off," she said as she began also stripping to just her panties,
garters, nylons and bra.
Doug was quick to follow suit. As soon as the two were shed of their
outer garments, Cindy handed one of the gowns to Doug while she placed
the other on her own body. Before climbing back in bed she turned down
the covers and then placed her small over night bag on the floor next
to the bed.
Doug laid back on the bed and realized he was extremely excited by the
wisps of nylon drapped across his body. Cindy knelt and stradled his
hips. The rustle and feel of nylon tricot was everywhere. She slowly
started rocking her hips back and forth and could sense Doug enjoyed
the smooth frictionless feel of the mingeling female garments.
Gently she reached beneath Doug's buttocks and pulled the tape
restraining his testicles. When she freed his semi-rigid cock she
rolled the front of his panties down and pulled his growing member out.
After she hooked the panties beneath his warm balls, she leaned over
and retrieved two soft vibrators from her night bag.
As Doug's penis became harder she rolled off of him and quickly shed
her own panties. Cindy then lubricated both toys and gently inserted
one in Dougs quivering anus. As she lowered herself upon his erection
she guided the other vibrator into her own anus.
"Oh baby," Doug moaned. He was so worked up from all the excitement of
the evening he knew he would not be able to hold back much longer.
Cindy knew he was near the edge. She sat up as straight as she could
and buried his cock deep within herself. Doug's hands were massaging
her anal cheeks as he worked the vibrator in and out of her.
Cindy used one hand to work the vibrator back and forth in Doug while
she kneeded his nipples beneath the bra he wore. With a violent
shudder Doug shot cum deep in Cindy.
She orgasimed twice as he spent his load. They both remained
motionless for an eternity and then slowly Doug started pumping in and
out of her again. Within seconds he had regained a rock hard rigidity
that Cindy knew would last throughout the night.
"Oh darling, darling," she moaned, "I love you so much."
1
2 _Doug_and_Cindy__________________________________________by_Karen_Shane___
Doug continued to pump as she rubbed her hands all over the nylon and
lace he wore. With each stroke of her hand the intensity of his
movements increased. The effect of lace was so great that Cindy knew
she had discovered a means to highten the pleasure both of them shared.
After they had both enjoyed countless orgasims they lay cuddled
together in a mixture of sensuous clothing. Cindy could not believe
the profound effect her suggestion of acting out a dream had had on
Doug. Or, for that matter, the effect it had on her. She slowly
drifted off to sleep vowing she would continue to live his dream.
IV.
Doug woke first. The realization of saturday morning at the motel
flickered through his mind. Awareness of the lingerie he wore flooded
his senses. Cindy was still snuggled up next to him and he enjoyed
looking at their two bodies dressed similiarly. He caressed her with
one hand while he caressed his own body with the other.
She woke slowly. She was vaguely sore and suddenly remembered why.
Cindy smiled as she opened her eyes and leaned closer to Doug to kiss
him. "Feel like a morning swim," she inquired.
Doug looked at her questioningly.
"I've got a really nice one piece suit for you. You'll love it!" She
said.
Cindy hopped from the bed and dashed to the bathroom. Doug sat up and
looked into the mirror. The wig was a little awry, but the make up was
intact. He adjusted the hair piece and flipped on the television set.
Cindy reappeared from the other room and tossed him the swim suit. She
had alreay pulled on a skimpy suit and had towels in her hand.
Doug examined the swim suit and looked puzzled. "How we gonna pull
this off," he asked.
"Strip down to just your panties, I've got another idea."
He did as she bid and then Cindy re-taped his flacid penis back the way
she had last night. "Now, pull on the suit and let's see."
Doug stepped into the fucia swim suit and pulled it up. The skirted
bottom hid any traces of his masculinity and Cindy helped him adjust
the blouson top. She then inserted a pair of breast prosthesis into
the built in bra of the suit and adjusted them in their confines.
"Well, maybe," Doug mused as he looked into the mirror. "But what
about the wig?"
"You'll just have to keep your head out of the water, or wear this swim
cap." Cindy said as she tossed him a rubber cap. She grabbed a pair of
towels from the bathroom and picked up the key from on top of the
television. "Come on, it's early. We'll have the pool to ourselves."
Doug followed her down the hall way and she was right, they had the
pool to themselves. After about a half an hour two skinny teenagers
showed up and began splashing each other in another corner of the pool.
Doug and Cindy decided they had better not press their luck so they got
out of the water and dried off.
With towels draped over their shoulders they headed back to the room
and were just crossing the second floor lobby when the dance partners
from the previous evening came up the stairway. Cindy saw the two men
and smiled. "Morning," she said as she recognized them.
The two men returned the smile and said "Good Morning" in unison. As
Doug and Cindy passed by them, the husky fellow that had danced with
Doug reached out and patted him on the ass as he walked by. Doug let
out a gasp while Cindy just chuckled.
"That's something I don't know how to handle." Doug told Cindy as he
closed the door behind him.
"You'll learn how to play the part." She responded while stepping into
the bathroom and adjusting the shower. "How about we shower together?"
Doug quickly joined her. When they had finished showering, Cindy laid
out a complete outfit on the bed for Doug. Standing with the towel
wrapped around himself, he carefully examined the items and then picked
up the sanitary belt and pad.
"That will probably be more comfortable than wearing tape all day. And
it'll be a lot easier to remove when ever you need to go to the
toilet." Cindy told him.
Doug nodded in acknowledgement and slowly stepped into the contraption.
Before pulling it up all the way, he pressed his testicles back and
then wiggled the pad into place. The straps rode high on his hips,
while the end of the belt disappeared into the cheeks of his ass.
Next, he donned the light blue nylon tricot panties and admired the
lace trim around the waist and leg bands. He marvelled at how the
sanitary pad produced a feminine pubic mound. He quickly picked up the
corset and was examining the garment while Cindy dressed.
He noticed it had heavy boned stays. The corset laced and hooked in
the back, so Doug slid the affair over his arms and positioned it in
place. Cindy stepped over and drew the laces tight and then hooked the
corset for him.
He slipped the silicone prosthesis in each cup of the corsets brassire
and then sat on the edge of the bed. While putting on the nylons and
fastening them to the garters of the corset, Doug could feel an
erection growing. He was thankful the sanitary pad held him secure.
Cindy tossed him an embrodiered lace slip and he quickly fitted the
sensuous garment to his body. "All of these clothes fit so nicely, and
they feel terrific. How did you ever get the right size in
everything?"
"You forget, dear, I've been buying your clothes for a long time. It
wasn't hard to convert your men clothes size to womens clothing." She
said.
Doug enjoyed the feeling of nylon swaying against his body as he
crossed the room to the closet. "Which dress is mine?" He said.
"Why don't you try the blue one hanging next to the outfit you wore
last night."
Doug removed a sky blue dress from the hanger and stepped into it. He
pulled the dress on and slipped his arms into it. As he adjusted the
puffy sleeves, Cindy zipped it up for him. He liked the mandrin collar
and the way the garment clung to his curves. "It's beautiful," he
murmered.
"I thought you'd like it." Cindy handed him her braclet watch and he
fastened it to his wrist.
She motioned for him to set at the dressing table and then carefully
began applying a light make up. "We'll skip the mascare for daylight
wear. I think this blue will match your dress." She said as she dabbed
a light powder blue to his eyelids.
She blended on small amounts of Cover Girl foundation and said, "We
don't want to over do it or that'll just call attention to you."
He picked up the lipstick she had set before him and slowly traced the
outline of his lips. Cindy was fastening a pair of dangling blue
plastic ear rings to his ears and Doug sat patiently observing the
process in the mirror. The illusion being created excited him and he
could feel his rock hard penis straining at the cotton pad.
When Cindy finished she handed him the wig and had him place it on his
head. She took a small brush and teased the hair piece until confident
it looked proper. "There, I think we're done."
Doug slid on a pair of woven straw sandles and fastened the straps
around his nylon encased legs. The feel of the nylons rubbing together
as he moved his legs about was too much for him. He hoped Cindy did
not notice as he shuddered and felt a warm liquid oozing between his
legs. He was thankful for the sanitary napkin and made a mental note
to take along a spare.
When he stood up, Doug took one last look in the mirror and couldn't
believe the picture of feminity that stared back at him. "Let's go."
Cindy said as she opened the door and waited for him to join.
"Where we going." Doug inquired as he stepped into the hallway with
Cindy.
"I thought we'd get some breakfast and then tour the art museum." She
answered.
They walked side by side to the stairs and then crossed the lobby to
the front door. Again Doug noticed that no one paid any attention to
them and he felt comfortable that he could masquerade so easily.
"I'll drive." Cindy said as she opened the passenger door for Doug.
They had not gotten out of the parking lot before discovering they had
a flat tire. "Damn," Cindy said, "of all times for this to happen."
She slammed the door as she started to walk around the vehicle to
assess the situation. Doug was comming around the front of the car to
join her when he heard, "Can we be of assistance ladies."
V
Doug and Cindy looked up to see their two dance partners nearing the
dissabled car. "Hi, I'm Dave and this is Dan." Said the fellow Cindy
had been dancing with. "We'll have that fixed in no time. Got a spare
in the trunk?" He inquired.
"Oh, thank you." Cindy said as she went around the car and placed the
key in the trunk. "I don't know what we'd have done if you hadn't come
along."
Dave removed the jack and wrench from the trunk as Dan set the spare
tire on the ground. While Dave began positioning the jack, Dan stepped
next to Doug and inquired, "How's Darla this beautiful morning?"
Dougs heart was pounding rapidly as he whispered, "Got a little case of
laringitist."
"Aw, that's too bad." Dan responded. "Maybe you'd like to join us for
breakfast. We were just planning to go down the street here to the
pancake house. How about it?"
Doug shot Cindy a glance and saw her perk up at Dan's suggestion.
"That would be wonderful, wouldn't it Darla."
Doug nodded meekly and wondered how he would handle the situation.
Dave had finished changing the tire and was putting everything back in
the trunk. "Why don't you park your car and we'll walk down to the
restuarant. It's only half a block away." He said.
Cindy agreed and backed the car into the slot. Dan offered his arm to
Doug and he limply placed his wrist in the crook of Dans arm. He was
glad he still had the false finger nails on as they gave his hands a
distinct female appearance.
Dave escorted Cindy as the two couples strolled down the side walk.
Doug began enjoying the attention Dan was showering upon him. He even
appreciated the way Dan held doors open for him and treated him as a
woman. He was glad Dan offered to order for him so that 'Darla'
wouldn't strain her throat.
Nearing the end of their meal, Doug felt Dan place his hand upon his
nylon covered leg and his eyes went wide open. Cindy saw the look in
her mates eyes and realized what must have happened. She smiled back
at Doug and said, "Enjoying yourself, Darla?"
Doug could only manage a week nod and continued to pick at the food on
his plate. Dans hand had gotten bolder and was slowly inching up his
leg. He could feel Dan toying with the top of his nylons and tracing
the outline of the garter.
Cindy saved him by announcing, "I need to use the powder room. Care to
join me Darla?"
Doug and Cindy quickly crossed the dining room to the womens rest room.
Once inside, Doug looked around and saw they were alone. "He's putting
his hands all over me. I don't know what to do."
"Don't be so worried honey. He can't do anything as long as we're in a
crowd. Enjoy it, and tease him a little. Surely you've been teased by
some girl in the past."
She made sense, Doug thought. "Well maybe," he started, "I just didn't
expect anything like this to happen."
"Have all the fun you want, 'cause when we go home we're the ones that
are together. I love you and I don't care what I have to do to make
you happy." Cindy stopped talking when another women entered the room.
She checked her own make up in the mirror as she handed Doug a tube of
lipstick.
They both returned to the table and Dave and Dan stood up to hold the
chairs for the women. Doug had not been seated for more than a minute
until he felt Dans' hand once again on his nylon covered knee.
As Dans fingers began creeping under the dress, Doug let his own hand
rest upon the thigh of his partner. Dan accepted the touch as a signal
and quickly slipped his fingers to the crotch of Dougs panties.
Feeling the sanitary napkin, Dan momentarily withdrew his hand and then
replaced it on the panty covered pad.
Dan slowly began applying pressure to the pad and rhythmatically
started rubbing it up and down. The feel of the moist pad against
Dougs flacid penis caused him to get an instant hard on and he found
himself becoming quite excited. As Dan continued to rub the pad, Dan
let his own hand drift farther up Dans thigh until he felt a familiar
bulge.
Cindy and Dave had lapsed into small talk, while it appeared Dan and
Doug were slowly finishing their meal. Doug heard Dave mention
something about stepping outside for a cigar and Cindy agreeing to join
him. Dan too quickly announced he would take care of the bill and Doug
looked up to see Cindy departing with Dave.
With the other couple gone, Dan increased the frequency of his
movements and Doug was breathing quite heavily. He grasped Dans bulge
with the tips of his false fingernails and pinched lightly as he began
stroking the stiffening member in time to the movements Dan was
applying to him.
Doug exploded warm, thick juices as he felt Dan shudder and cease his
activities with the pad. Doug squirmed slightly to allow the last few
drops to drain from him into the awaiting sanitary napkin. For the
second time today he was glad the pad was in place as he with drew his
hand from Dans crotch.
Doug had a contented smile on his face and noticed Dan was wearing a
sheepish grin. Both glanced down and saw a small spot appearing as the
tent shaped fabric of Dans trousers began to sink back down. "I guess
I'd better head back to the room." Dan said meekly.
He left some bills on the guest check and then escorted Darla from the
restuarant. Cindy and Dave appeared to be deep in an animated
conversation and nearly missed them as they came out. They all quickly
returned to the motel where Dan bid farewell as he rapidly crossed the
lobby and bounded the stairs two at a time.
Dave looked questioningly after him and then turned and shrugged to
Cindy and Darla. "I guess I'd better go make sure he's alright. Will
we see you girls again?"
Cindy smiled at Doug and then said, "We'll be in the lounge again
tonight. Perhaps we can slip away from our husbands again. They're
out playing golf now, and are usually too tired to go out when they've
completed eighteen holes."
Dave bid them farewell and then departed. "What ever happened after we
left?" She inquired of Doug.
"I think I have to go up to the room for a minute too. You said to
enjoy myself, and well, I just did what he did to me."
Cindy chuckled to herself and thought outloud, "You sure learn fast."
They returned to the room and before Doug had a chance to replace the
soiled napkin, Cindy crossed the room to him and gently pushed him onto
the bed.
Caught unaware, Doug fell back on the bed as Cindy bounced on to it
next to him. She rapidly slid her hand under his dress and began
massaging the panties against his napkin. He instinctively parted his
legs for her and felt the wettness from his earlier excitement.
Cindy hiked her own dress above her thighs and straddled Doug with her
head facing his feet. She bent over to reach her night case and he
nuzzled his face against the fabric of her panties. She continued
massaging the sanitary pad against his growing erection as she pulled
one of the toys from her case.
Doug could feel his penis growing as he buried his face in Cindys
pantied rump. He began to nibble on the tricot barrier and could feel
her vaginal lips slidding beneath the soft fabric. His own panties
strained at the pressure of his emerging hard on pushing against the
pad Cindy was massaging.
Cindy slid the leg band of his panties aside and lubricated the object
in her hand with the dampness from his pad. As he continued to tease
her with his mouth against her own panties she slid the soft, firm
vibrator into his anus. She slowly worked the toy in and out as she
increased her movement of the sanitary napkin against his rigid cock.
Doug felt like he was in heaven. He nibbled harder and caught her lips
between the fabric of her panties as she plunged the vibrator back and
forth in his anus. The sensation of nylons and tricot intermingling
with the constraint of the corset and her actions on his body were over
powering.
Cindy knew he was nearing the moment and she released his cock from the
pad which held it. It pointed straight in the air as she climbed from
his body and quickly stripped her own panties as quick as she could.
She turned and positioned herself above him and then lowered her body
to his. Her moistness engulfed him as she continued to plunge the
vibrator in and out.
Garters snagged against garters as lace mixed with nylon and nylon. He
exploded like never before. She quivered, then shuddered and exploded
too. Wetness drained everywhere as they continued to pump feverishly.
And then they were motionless.
Cindy sat breathing heavily as Doug grasped for air. The vibrator was
buried deep within him as he remained buried deep within her.
Moments later, an eternity, he slowly felt himself fading. As his
penis returned to a flacid state, she slowly withdrew the vibrator.
Cindy contracted her muscles and he popped from within her. At the
same instant she totally with drew the toy and dropped it to the floor.
"We've never, I mean never, had sex with such urgency. I think it was
great!" Cindy said as she got up from the bed. She picked up her
panties and stepped back into them as Doug sat up.
He could not say anything. He knew she was right. He got up and
headed for the bathroom after picking up a fresh napkin from the box
Cindy had in the suitcase.
"Now you really see why the garters go underneath the panties, don't
you." Cindy called out to him.
Doug only responded by flushing the toilet and completing the task at
hand. Seconds later he stepped from the other room and joined Cindy on
the edge of the bed. "I guess the museums out for this morning. What
other little surprises did you have in mind?"
"Oh, I've got a little idea in mind you might enjoy."
Cindy got up from the bed and opened the door. Doug followed her out
and they both headed for the car. She drove for a few minutes and Doug
realized they were headed downtown. She circled one block a few times
and then pulled into a vacant spot in front of an adult book store.
Doug smiled.
She opened the door for him and they both stepped into the store. It
was still early in the day and few other customers were among the racks
of magazines and video cassettes. Cindy walked from one isle to the
next until she spotted the section containing literature on female
impersonators. Doug stepped next to her as she picked up one magazine
from each holder and began cradling them in her arm.
After she was sure she had one of each selection she wandered around a
bit and then settled in front of the counter containing toys of every
description. She selected a few items and the gaunt male clerk
nonchalauntly dropped them into a bag. She paid him and then turned to
find Doug still browsing through the titles she had made her choices
from.
Cindy caught his attention and signalled him that she was ready to
leave. Doug replaced the magazine he'd been thumbing through and
accompanied her to the car. "I got one of each and we can look at them
later back at the motel. For now, let's head to the mall. I have a
few more things to pick up and we can grab some lunch at one of the
lounges there."
Doug was only to happy to be dressed as he was and didn't really care
where they went. He enjoyed the breeze as it wafted gently through his
wig and chilled his lace clad body. The trip to the mall passed
rapidly as Cindy drove among the week end congestion.
She led him through the window shoppers and squalling children to a
womens longerie shop at the end of one passageway. It only took her
seconds to scoop up oodles of pastel colored panties and deposit them
in Dougs arms. She selected a few more packaged panties and dropped
them on top of the growing armful held by Doug.
"When we get home, I'm going to get rid of all your cotton underwear.
If what's happened to us in the last two days is caused by these, I
intend to keep you well dressed from now on."
Doug caressed the items he held and considered the words she said. He
could feel his manhood growing and realized what she was telling him
was the cause for it. As he walked behind her the constant strain of
the napkin against his cock and the thought of such beautiful under
garments caused him to become even harder.
Cindy picked out a couple of varieties of teddies and panty slips and
also handed them to Doug. His arms were so full he had to get a basket
from next to the counter to carry everything she was getting. When he
returned to her, Cindy handed him another armful of silk and lace.
The basket was overflowing when she finally decided to add a few
brassires to his growing collection of feminine attire. As he waited
patiently while Cindy paid for the items he discovered he was
unconsciously squeezing his thighs together rythmatically and was
causing his rigid cock to strain even more at the pad.
He watched the young teenaged clerk carefully folding and placing the
wealth of silk and nylon in packages and he pressed his thighs tightly
together one last time. He felt the warm, damp liquid exploded from
within and fill the waiting sanitary napkin. For yet another time
today, he was greatful for the security of the pad and hoped no one
noticed the little shudder he gave as the final drops spent from his
penis.
They left the store and wandered among the mall. Doug savoured the way
his softening member slid among the lubrication of the pad and he
likened the feeling to that of being buried deep within Cindy.
They enjoyed a leisurely lunch in one of the mall restuarants and then
continued window shopping until deciding to return to the motel. Cindy
returned to the car for the last of the days purchases as Doug sank
into a chair and absently flipped on the television set.
When Cindy returned from the car, she found Doug had fallen asleep in
the chair with his wig slightly awry. She quietly removed it and then
began sorting items from the days shopping spree. After she had packed
everything away, she took a hot bath and then prepared one for Doug.
She awoke him with a kiss and said, "I've got a nice hot bath ready for
you. Why don't you relax in the tub awhile and I'll pick out some
things for us to wear tonight. "
He nodded and groggily made his way to the bathroom. He slipped out of
the blue dress before going in the bathroom and drapped it over a
chair. He kicked off the sandels and then padded into the bathroom
clad in his dainty underwear.
He let the slip fall to the floor as he began unfastening the garters
and removed the nylons. The corset was a little difficult to remove by
himself, but he managed to shed to garment and stood for a second
looking at the reflection of his pantied backside in the mirror. He
could see the indentation of the sanitary belt beheath his panties and
suddenly realized it was still damp.
He quickly peeled off the remaining garments and then slid into the
tub. The hot, bubbly liquid comforted him as he picked up the safety
razor Cindy had left on the side of the tub. Even though his legs did
not need it, he slowly drew the razor against them and made sure they
were closely shaven. The feeling created by the ritual caused him to
acknowledge a deep feminine urging from somewhere within himself.
Doug pondered the emotions welling up and then asked Cindy, "Were you
serious about what you said when we were in that one store today?"
"Definetely," she responded. "The way soft women's clothing has
excited you the last two days is fantastic. I intend to see that you
remain as happy as you've been this weekend. Besides, who will know?"
He had dried off, and wrapped the towel around himself the way Cindy
usually did, high on his chest. He paused and gazed at his reflection
in the mirror. With all the make up washed off, you didn't notice his
eyebrows had been plucked and took on a feminine appearance, he
thought.
Cindy came into the bathroom and began preparing a bath for herself.
"I've set everything out for you on the bed." She said. "I'm going to
get cleaned up while you dress, and then I'll slip into something and
we'll go down to the lounge again for supper."
Doug left her alone while he went out to check what she had selected
for him. He found the sanitary napkin and belt on top of all the
articles she had piled on the bed and he quickly stepped into the
garment and tucked his maleness between his legs. Before pulling the
pad into place, he sprinkled some of her fragrant powder on it and then
snuggled it against his soft cock.
She had chosen a deep plunging front closure brassire for him and he
had little difficulty fastening the bra. He admired the way the clasp
fitted securely behind a pretty little bow of ribbon and the mounds of
decorative lace on the cups of the bra. Before putting on the matching
garter belt, he slid the prothesis in place and marveled at the way
they giggled as he moved about.
He fastened the lace belt around his waist and then decided to paint
his toe nails with a shade of nail polish that would match the false
nails he still wore on his fingers. After completing the task, he put
on the mint colored slip Cindy had left for him and then sat on the bed
while the polish dried.
Cindy stepped out of the bathroom and detected the aroma of nail
polish. "Oh, good idea." She said as she dropped the towel from around
her and slipped into her own brassire. Doug quietly noticed she had
selected matching intimate apparal for herself and he was pleased they
could share such lovely attire. As she pulled on her panties, she
said, "Why don't you sit down over here and I'll fix your make up."
He obediently took the chair next to the dressing table and Cindy
expertly applied a light cream foundation to his face and neck. "Now,
blend it in with this pad." She said as she handed him a small foam
make up pad.
Doug smoothed the foundation until he could not detect a line between
the make up and his skin and then Cindy started applying a frosty eye
shadow on his eye lids. After she had finished each eye she handed him
the mascara and watched as he brushed the dark cream on his lashes.
Next, he picked up the lip stick she had placed before him and
carefully traced the outline of his lips.
She used a small brush and dabbed a light coating of blusher on his
cheeks and then took an eye brow pencil and rounded out the contour of
his brows. Doug picked up her perfume and placed a small drop behind
each of his ears and on each of his wrists.
He returned to the side of the bed and put on his nylons and then
pulled on a pair of dainty, pretty hip huggers made of lycra spandex.
He smoothed and brushed the slip in place and could feel the urgings
welling up within himself. The soft fabric clunge to his body and the
cool feel of lace against nylon excited him.
Cindy tossed a pair of opened toed high heels on the floor in front of
him and he slipped his feet into them. She had thoughtfully selected
large heels so that he would not have too much difficulty in learning
to walk in them. He tested his ability to manuver with the heels by
strutting around the room.
He noticed the heels caused his calfs to appear even more feminine and
he stood admiring his legs for a minute. Cindy brought him a soft
woolen skirt and helped him step into it. She fastened the clasp and
then handed him a matching mohair sweater. Doug slid the sweater over
his head and adjusted the cowl neck to fall partially over his back.
Cindy gave him a large beaded necklace and ear rings to put on while
she finished dressing and Doug stepped over to the mirror to accomplish
the task. When he finished putting on the jewerly he picked up the wig
and placed it on his head. He used her styling brush to fluff it out
and brush a few stray hairs in place. Cindy smiled at how naturally he
performed the deed and noted how beautiful he looked.
Without saying anything to each other, they picked up their purses and
left the room. Cindy dropped the key in her purse as they started down
the hallway toward the lounge. Doug noticed the heels caused him to
sway slightly as he walked and his skirt rippled rythmatically as they
descended the stairs to the lobby.
A few guest glanced casually at them as they crossed the lobby and
entered the shadows of the lounge. Cindy spotted Dave and Dan seated
at a far corner of the adjacent dining room and noticed Doug had also
seen them. Dan had risen from their table and was making his way
toward them. "Looks like we're in for a little more fun." She wispered
to Doug.
"Good evening Cindy. How's the throat Darla?" Without waiting for a
reply, Dan said, "How about joining us for diner. We just got here and
haven't ordered yet." He took Doug by the arm and began escorting the
two to their table. Cindy walked behind the two and chuckled inwardly
at the way Dan had placed his arm around Darla's waist.
Dave stood up and held Cindys chair for her as Dan assisted Darla in
taking a seat next to him. "I take it your husbands won't be joining
you for diner this evening." Dave said as he took his own seat again.
"They've got some kind of business meeting and should be returning
around ten o'clock or so." Cindy said. She knew that would give them
enough time for a little fun, but would still provide Doug with the
excuse he may need later.
"Well, at least let us have the pleasure of your company until then."
Dan said as he placed his hand on Darla's knee.
Doug smiled. He we go again, he thought to himself. At least Cindy
had put a time limit on it, he thought, and he was grateful for that.
He started to whisper something to Dan, but the band began playing a
loud, fast rendition of some familiar song and all chance of
conversation was lost.
Somehow, Dave managed to place orders for them all with the waiter
standing at their table now and Doug heard him order a large bottle of
champagne. The waiter disappeared shortly and then returned with a
cart bearing the beverage and fine glasses. He watched as Dave sampled
the bubbly liquid and nodded approval. Glasses passed around and they
all shared the champagne as Doug felt Dan's hand begining its upword
trek.
Doug had finished a third glass of champagne by the time Dan had his
fingers toying with the edge of the sanitary pad. In an effort to keep
his wandering fingers from exploring beyond that point, Doug placed his
own hand on Dans crotch and could feel the mans soft bulge respond to
his touch.
The waiter appeared with their dinner and Doug coyly brushed Dans hand
from between his legs. He crossed his legs to prevent further advances
from Dan and enjoyed the meal before him. Dan ate feverishly and they
all drank heartily from the dwindling supply of champagne.
Dave had managed to signal the waiter for another bottle as they
finished their meals and he quickly replenished the empty bottle as he
cleared a few items from the table. Doug was thankful they were so
close to the band and could not carry on conversations at the table.
He was also begining to feel a little gidish from all the champagne he
had consumed and hoped he wasn't getting careless in the illusion he
was trying to maintain.
Somehow the four managed to deplete the new bottle of champagne in less
than two songs from the band. Dave signalled the waiter once again and
then signed the check and motioned for them all to leave.
Dan escorted him from the lounge as Cindy took Daves arm and
accompanied them to the lobby. "Why don't we stop up to our room and
have a quick night cap before bidding ado?" Dave said to the group.
Doug looked at Cindy and found her agreeing to the suggestion. He
wasn't sure what to do and was quickly hurried along by Dan's insistent
pressure on his waist. They crossed the lobby to the elevator and were
wisked to the second floor before he had a chance to think of anything.
They entered Daves room and soon discovered the two were sharing
adjoining rooms. Dan opened the small passageway to his room and
quickly disappeared from sight. Dave offered Cindy a chair by the
window as he picked up the plastic bucket from the sink and said he
would fetch some ice. Alone for a second in the room, Doug looked
questioningly at Cindy and realized she too was feeling the effect of
the champagne.
Dan returned from the adjoining room carrying a small bong and stopped
in front of the television set to light the marijuana packed tightly in
the bowl. He drew deeply from the mouth piece and then passed the bong
to Doug. Darla accepted the bong and hesitated briefly before inhaling
the rich pungent smoke into his lungs. He passed the bong to Cindy and
she too inhaled deeply on the mouth piece.
Dave returned with the ice and rapidly mixed drinks for them all before
joining in the activites already in progress. Cindy enjoyed watching
Doug squirm nervously in his feminine attire as Dan began running his
hand up and down Darlas back. She stood up and crossed the room to the
television and flipped it on.
"I'm afraid it may be the wrong time for either of us to fully
demonstrate our appreciation, but," she said as she stepped over to the
light switch and turned it off, "if you'd care to lay down on the bed,
perhaps we can at least show you a little bit of our gratitude."
Dan and Dave needed no further prompting. They both got on the bed and
laid down. Cindy took Dougs hand and pulled him along as she neared
the bed. She let his hand go as she knelt on the bed next to Dave and
began unbuckling his trousers. Doug hesitated and then mimiced Cindys
actions by unbuckling Dans slacks.
He watched her roll Daves cotton briefs down and expose his growing
cock. Dans rigid member was already straining at his own briefs as
Doug pulled the waistband over the stiff, erect cock. He saw Cindy
brush her hair away from her head as she lowered her lips toward the
now hard cock and realized what he must also do.
He wrapped his hand around Dans cock and began massaging it as he
lowered himself to a seated position on the bed. Cindy was now taking
Daves organ in her mouth as Doug lowered his head to Dans eager cock.
He placed the tip of it in his mouth and let his tounge dance upon the
head of the cock as he continued his stroking motions on the long
shaft.
Doug could taste a hint of salt as he realized Dan was becoming
extremly excited. He let the shaft bury deeper into his mouth and
pressed his lips firmly around it. His hand moved down from the shaft
and cuped the two hairy balls as he began slidding his lips up and down
the thick cock. He found that his own cock was begining to strain
against the sanitary napkin and he started squeezing his thighs
together as he had done earlier today at the store with Cindy.
Doug gribbed the sacks of skin in his hand tightly as he continued to
pump his lips up and down the shaft. He could feel Dan tensing and
knew it would only be seconds before he exploded. Doug sensed his own
urgency and locked his legs together as Dan began spending his load.
He felt the warm liquid hitting the roof of his mouth as his own
orgasim spilled into the napkin. He took everything Dan offered and
Doug_and_Cindy__________________________________________by_Karen_Shane__3_
then traced the length of his shaft with his tounge as Dan laid
motionless.
He felt Cindy place her hand on his shoulder and looked up to see her
headed through the adjoining doorway. He quickly followed behind and
saw her pick up a small plastic bag from the dresser as she opened the
door to the hallway. He pulled the door behind him as she said, "Small
price for them to pay." And then saw her drop the plastic bag of
marijuana into her purse.
They quickly made their way down one flight of stairs and through the
hallway to their room. Doug was thankful they had not given their room
number out as he locked the door behind them. Cindy was stepping out
of her dress as he drew the curtains closed.
"I'm going to run down to the store and get a bottle. Why don't you
get comfortable and I'll be right back." Cindy had pulled on a pair of
levi's and was just slipping into a sweat shirt when Doug realized what
she had said.
She left before he could say anything, so Doug lit a cigarette and
relaxed on the bed for awhile. He picked up the package of magazines
they had bought earlier and began thumbing through them absentmindedly.
The sight of so many she-males brought him to a state of ecstasy
quicker than he thought possible.
He gazed at the glossy color pictures of professional female
impersonators and could feel his cock sliding in a sea of lubrication
as it grew larger. The pictures of such beautiful men draped in silken
finery brought him near the edge and Doug put the magazines down as he
realized he was breathing heavily. He got up from the bed and shed the
skirt and angora sweater he had been wearing.
After hanging up the garments he let the slip slid down his hips and
fall billowing to the floor. He picked up a pegnoir set Cindy had left
on top of a suit case and put the frilly nightgown on. He then donned
the matching sheer robe and laced the gown at his waist.
Doug returned to the bed and had just laid down when Cindy returned
carrying some sodas and a bottle of rum. She deposited the containers
on the counter next to the sink and grabbed the plastic bucket for ice.
While she went for ice, Doug mixed two drinks and awaited her return.
"Oh good. I see you found the gown I left out for you. Pretty isn't
it?" Cindy said as she plopped some ice in each of the glass Doug held.
"Yes. I like it."
Cindy placed a box near the bed and then quickly peeled off her own
outer garments. She stood near the bed as she up ended the glass and
drained the last drops of rum and coke from her glass. Doug mixed her
another as she dropped to the bed and then he too joined her on the
bed.
"Lay on your tummy, here." Cindy said as she patted the mattress next
to her. Doug did as she asked and then felt her hand as she slowly
stroked the back of his leg. Cindy allowed her hand to toy with his
the edge of his panties as she reached into the box next to the bed.
She withdrew a soft, firm rubber penis with a strap on it. She stood
next to the bed and strapped the artificial devise to her hips and then
knelt on the bed next to Doug.
Before doing anything else, she pulled another rubber penis from the
box and slid the leg band of her own panties aside. She inserted the
second dildo in herself and released the leg band of her panties so
that the crotch of the soft fabric held the toy in place.
With the rubber penis dangling from the straps around her hips, she
crawled between Dougs legs and leaned forward. The tip of it pressed
against the sanitary napkin and she reached down and pulled his panties
down. She pulled the napkin aside and then pressed the head of the
shaft against his anus.
Dougs own erect cock strained at the pad as he felt Cindy pressing
harder with the dildo. As she rocked back and forth the rubber cock
slid into his ass and he raised his hips instictively to allow her
better access.
Cindy drove the false appendage deep within Doug and could feel the
second dildo deep within herself. He let out a gasp as the shaft
buried deeper and then felt Cindy sink into a rhythm of pumping the
dildo in his ass.
As she pressed the rubber cock into him, Dougs own cock slid among the
lubricant he had previosly deposited on the sanitary napkin. With each
thrust she made, he pressed back against her while pressing his own
thighs together.
Cindys tempo had increased and she began massaging her clit with one
hand. Dougs breathing matched the frequency of Cindys thrusts and he
felt himself explode as she shuddered rapidly and plunged the dildo as
deep as she could.
She sat there a long while with the dildo buried deep in Dougs anus and
then unstrapped the device from her body. She rolled over next to him
and slid the other dildo from between her own legs. She dropped it to
the floor and then slowly pulled the rubber cock from Dougs ass and
dropped it next to the first.
Spent and exhausted, they both found sleep a welcome companion. Even
deep asleep, Doug could sense the frilly garments clinging to his body
and he retained a nocturnal erection that slid among his own juices as
he ocassionaly tossed and turned.
Morning came too soon, but Doug awoke with a sense of urgency and
rapidly became aware of the straining pad between his legs. Cindy was
still asleep and he let his hands drift over the soft gown draping his
body. The feel of nylon tricot against his body excited him even more,
so he rolled his panties down and freed his throbbing penis from its
prison.
As Cindy slept, he found himself manipulating his cock through the gown
and realized he was going to climax soon. Not wanting to be
apprehended, he quickly pushed his manhood back into the sanitary
napkin and rolled the panties back up. Just as he finished adjusting
the waist band of the hip huggers he felt himself exploded once again
into the napkin. The warm, moist liquid ran from his cock and trickled
between the napkin and his buttocks. He enjoyed the sensation and laid
motionless while the warmness crept deeper and traced the contours
created by the pad against his ass.
When he could no longer feel the warmth, Doug quietly got up and padded
off to the bathroom. He adjusted the shower and then ever so slowly,
slipped the pegnoir set off and admired the reflection of his scantily
clad body in the mirror. He had to admit that he really loved the
feminine under garments he was wearing. With great reluctance, he
slowly removed the nylons, garter belt, panties, bra and sanitary
napkin and stepped into the shower.
He was just finishing drying off when Cindy woke and joined him in the
bathroom. "You should have woke me sooner. We haven't got long before
check out. I'm going to take a quick shower too, and then we'd better
get going. I'll pick out some things for you in a minute, why don't
you try putting on your make up." She didn't wait for a reply as she
stepped into the shower and realized she hadn't felt so refreshed in a
long time.
Doug followed her suggestion and began by applying a light foundation.
He remembered what she had taught him earlier about not over doing it,
so he sparingly applied the foundation and then blended it in. He put
the mascara on lightly also and then carefully used an eyebrow pencil
to fill in his brows. He selected a pale color lipstick and was just
finishing with it when Cindy popped out of the bathroom. As she busied
herself with choosing various clothing for the two, he finished off by
dabbing a light coating of eyeshadow to his eyelids and then
complimented himself as he stared at the reflection in the mirror.
He crossed over to the bed and picked up the fresh sanitary napkin
Cindy had placed on the top his clothing pile. With a deftness usually
reserved to an art practiced for a long time, Doug slipped into the
sanitary belt and threaded the napkin in place. He tucked himself away
and adjusted the napkin to hold him secure as he picked up the long
line brassire and slipped it over his arms. Somehow he managed to hook
all eight of the bras hooks and noticed that the increased pressure
from the long line bra caused his loose flesh to swell and create an
illusion of cleavage. He quickly tossed out the notion of doing
without the prosethisis and slipped the artificial breast in place.
Next, he pulled on the full cut panties and picked up the girdle Cindy
had selected for him. He struggled to pull the constraining item on,
but soon had it adjusted properly. He followed by slidding into a knee
length slip and then sat on the bed to put on his nylons.
He completed the outfit with a simple cotton blouse and a dark, knit
skirt that she had also laid out on the bed. When he had fastened the
clasp and pulled the zipper up, he put on the same woven sandles he had
worn the day before and picked up the wig he now thought of as his own.
Cindy had already taken one load of luggage to the car, so Doug picked
up a few more of the things in the room and carried them down to the
car. Cindy passed him in the lobby and told him she would get the last
of their belongings and be right back.
While waiting in the car, he picked up one of the magazines Cindy had
purchased yesterday and began thumbing through it. He read with
interest, the letters submitted by readers describing how they had been
introduced to the world of cross dressing. As he read the detailed
accounts he could feel his sanitary napkin straining against his
growing erection.
Cindy returned with the last of the luggage from the room and they
started for home. "I really enjoyed this weekend." Doug confided in
her. "In fact, I kind of hate to see it end."
"Oh, it's not ended. When we get home, it's just begining." Cindy
replied.
Doug pondered her words as she manuvered through the Sunday traffic.
The pleasure he experienced dressed as a woman was over whelming and he
savoured the drive home. Ocassionally he would shift in the seat to
glimpse something out the window and would quickly be reminded of the
tight girdle and nylons he wore. Doug could'nt imagine being happier.
Cindy pulled into the underground garage at their apartment and the two
women stepped from the car. A quick ride up the elevator and short
walk down the hallway brought them to their own apartment. As he
closed the door behind them, Doug could'nt help but reflect how his
whole attitude and outlook had changed from just a few days ago when he
stood in the same spot.
Cindy had disappeared into the bedroom and Doug headed that way to see
what she was up to. When he entered the room he saw her standing
before his dresser with a couple of drawers pulled open. He stood
hypnotized as he watched her scooping out handfuls of his male cotton
underwear and drop them in a paper bag. She really was doing what she
said she would, he realized.
"From now on, you'll wear pretty lace panties under everything you
wear. When you're home on the week ends, and after work, I'll expect
you to wear at least a bra, too." Cindy told him as she began putting
oodles of pastel colored frilly garments in the now empty drawers.
Her words, and the thoughts cascading through his mind, caused Doug to
become acutely aware of the stiffness returning between his legs. He
watched her pick up the bag full of male underwear and carry it out to
the trash chute in the kitchen hallway. He knew she ment what she had
just said as he watched the bag disappear down the chute.
Cindy busied herself with the coffee maker and Doug sat down on one of
the bar stools at the breakfast bar. She finished pouring the water in
and said, "In a couple of months, I'll be able to style your hair and
you won't need a wig any longer. Of course, you can use any of the
ones I have now until then."
"I noticed in one of those magazines that there are some clubs and
organizations in the area that offer support for couples like
ourselves." Doug said tentatively, "Perhaps we could investigate them."
"If you like, but from now on, I intend to see you become my sister as
well as my husband." She said. "It will be wonderful being able to
share so much more with you. I only wish we'd have discovered this
sooner."
The aroma of caffine drifted through the kitchen so Doug retrived two
cups from the counter. He had kicked off the sandles in the bedroom
and marveled at the way his nylon covered feet felt as he crossed the
linolium floor. The tug of the nylons against his girdle excited him
and he could feel the elastic stretch slightly as he walked.
"Let's go try on a few things I think you might like. I've got a lot
of cloths in the back of my closet that might fit you just perfect."
Cindy said as she accepted the cup of coffee Doug held out for her.
They returned to the bedroom and she quickly started tossing various
articles from her closet onto the bed. Doug watched silently for a few
seconds and then unhooked his skirt and stepped from it. He shed the
blouse he had been wearing and picked up a black one piece jumpsuit
from on top of the growing pile.
He managed to zip up the jumpsuit without assistance and then noticed
the girdle created unsightly lines through the skin tight fabric.
"You'll have to learn to wear different types of underwear depending on
what you'll be wearing." Cindy said as she noticed him checking his
appearance in the mirror. "Panty hose would be best for something like
that."
He shed the jumpsuit and tried on a few more garments. He noticed that
with every new piece of feminine apparal he tried on, he became more
excited and the straining at his sanitary napkin increased. He stepped
out of the house dress he had just tried on and stood in just the
matronly under garments Cindy had provided at the motel this morning.
Without having to say anything to her, Cindy looked deep into his eyes
and then slipped out of her own skirt and blouse. She crossed to the
bed and brushed the pile of clothing aside as she laid down. Doug
quickly joined her and as he began kissing her deeply he felt her
unzipping the girdle at his waist. She rolled the heavy garment down
his hips and then he assisted by removing it with the nylons still
attached.
The slip pulled taugnt against his panty clad ass as he rolled back
toward her and embraced her once again. The feeling of her breast
pressed hard against his own bra clad chest caused him to become more
excited and he loved the sensations shooting throughout his body.
Quite by surprise, Doug felt her pressing an anal plug into his ass and
he welcomed the sensations it created. Cindy buried the plug as far as
she could and then pulled his rigid cock from beneath the napkin and
through one leg band of his panties. He wasted no time in mounting her
and thrusting his eager cock deep between her open legs.
With each penetrating thrust, Doug could feel the plug within himself.
Cindy was becoming more excited and he could feel her hands pressing
hard against the long line bra hooked behind his back. He continued to
pump deep into her and then felt her move one hand down to his
quivering asshole. With each thrust of his cock deep within her, Cindy
pressed the plug with equal intensity.
His movements increased in frequency corresponding to the pressure
Cindy placed upon the plug. Within seconds he exploded dynamically and
felt her shudder with her own climax as she pushed the anal plug as
deep as she could.
They lay spent and coupled together for long moments as each tried to
regain their breath. After a few minutes Doug could feel himself
loosing rigidity and withdrew to lay at her side. He saw that deep
satisfied look on her face and knew she had needed him as much as he
had wanted her.
"This is the reason I plan to keep you in skirts." She said. "You're
just so much more sexually active, I'm going to see to it that you
always have lace and nylon on your body."
Doug smiled to himself as he trudged off to the bathroom for a quick
shower. She was right, he thought to himself, the frilly garments did
cause him to need her more. He stripped naked and relaxed as the hot
water streamed down his body. Moments later, he dried off and returned
to the bed.
Cindy had put all of the clothing away so he pulled open one of his
drawers and fingered the fine silk now his to choose from. He selected
a pair of floral patterned hip huggers and a matching whispy floral
brassire. He tossed the frilly underwear on the bed and then took out
a new sanitary belt from the box she had put in his drawer.
The new belt was more like a string bikini and it took him a second to
discover how to thread a napkin in place. He quickly learned how to
adjust the belt and then started to pull it in place. He hesitated for
a second after tucking his flacid penis back, and then picked up a
bottle of hand lotion on the dresser and traced a small line of lotion
along the inside of his pad. As he pulled the napkin securely against
his body he could feel the cold lotion come in contact with his penis
and then felt the lotion spread along the shaft of his manhood. As he
walked over to the bed to retrieve his bra and panties he could feel
the slippery lubricant and it reminded him of the feelings he had
experienced so often the last couple days.
He quickly pulled on the hip huggers and slipped into the flimsy bra.
After hooking the clasps behind his back he decided not to use the
prosthesis and went instead to the closet. He selected a sleeveless
tank top blouse and a pair of pink stretch shorts to wear. He put on
the pretty apparel and then joined Cindy who was now watching
television in the living room.
Fin